Travel to Bermuda

How to make the most of your time on the tropical British island

It was the high-prep mid-'80s when we teenagers (I, my older sister, and two stepsisters) would visit my English granddad in Bermuda. Off the coast of North Carolina and less than a three-hour flight from Boston or New York, the islands are, oddly, a British territory. In some ways, a stay there felt like a time-machine trip to the raj. It's no surprise that my grandfather, born in India in 1906 and a classic adventurer type (sailboat racing across the Atlantic; barnstorming), as a 70-year-old widower remarried and set up for the season (April through October) in Bermuda, known for its shipwrecks, pirates, mischievous triangle, and golf.

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For these stays at the fascinatingly adult cocktail-hour world of Fairwinds, his new wife's colonial house, we borrowed his madras shorts and wore Lanz of Salzburg flannel nightgowns and L.L.Bean Blucher Moccasins. But Bermuda had our preppiness trumped with its quaint limestone-walled roads and coral pink houses.

Fast-forward to the present. I recently returned to Bermuda with my sister for a rest, after a few crazy months promoting my travel book, Gypset Style. I was hoping to find the Bermuda of my youth's magical out-of-time bubble still unpopped. I did. Like a properly bred matron, Bermuda has both retained its Slim Aarons–era innocence and strolled elegantly into the now. Back then, we would whiz wild on mopeds, beach-hopping and flirting, and in the evening, string on pearls for dinners with our grandfather at the staid Coral Beach or Royal Bermuda Yacht clubs, where we would shake extra black rum and sherry pepper into our chowder to catch a buzz. The subtropical island still feels like one big country club. Michael Bloomberg, Silvio Berlusconi, and Catherine Zeta-Jones and Michael Douglas all keep relatively ungaudy homes here. There's hardly a bad view to be had, and somehow the whole place—from Somerset Village on the western tip to the settlers' town of St. George on the eastern end—smells like freshly cut grass. Even the sand is pink, possibly in a nod to the "smart casual" dress code.

This time, we still whizzed around on mopeds, discovering Chaplin Bay, a hidden cove that coincidentally shares our last name, and got fashion-inspired by the unabashedly pink-clad island establishment in the city center at lunch hour. But instead of bunking at Fairwinds (my grandfather died in 1991), we stayed at the terrificially glamorous new Tucker's Point Hotel & Spa, where we could actually partake in the cocktail-hour Dark 'n Stormies with the rest of the grown-ups. It was a much- needed reminder that the charade of adulthood can sometimes be a winning game.